Country music star Toby Keith has been captivating audiences for over two decades with his blend of traditional and contemporary country sounds. Known for his patriotic anthems and party songs, Toby has amassed an impressive catalog of hits over his career. But what songs is the famous Oklahoman really known for? Let’s take a look at some of Toby Keith’s most popular and iconic tunes.
“Should’ve Been a Cowboy”
Released in 1993 as Toby’s debut single, “Should’ve Been a Cowboy” immediately launched him into stardom. The song, which features Toby’s smooth baritone and lyrics lamenting missed opportunities, topped the Billboard Country Songs chart for several weeks. It was the most-played country song of the 1990s and remains Toby’s signature tune. “Should’ve Been a Cowboy” earned Toby Keith the title of Billboard’s New Male Artist of the Year in 1993 and set the tone for his unique outlaw-meets-traditional country style.
“How Do You Like Me Now?!”
This defiant 2000 single is considered one of Toby’s most popular songs. It tells the story of a man who was mocked and underestimated in high school but goes on to achieve success as an adult. “How Do You Like Me Now?!” spent five weeks at number one on the country charts and even crossed over to the mainstream pop charts. The catchy chorus and clever lyrics helped make the song an arena-rocking fan favorite at Toby’s live shows. It epitomizes his bold, in-your-face attitude and cemented his status as a major force in country music.
“Courtesy of the Red, White and Blue (The Angry American)”
Released in 2002 shortly after the 9/11 terrorist attacks, this patriotic anthem resonated strongly with country fans. Co-written by Toby Keith, “Courtesy of the Red, White and Blue” expresses pride in American values and military might. It originally included references to kicking “a**” but Toby cleaned up the lyrics for radio. The song was a number one hit, making Toby the face of country music patriotism in the early 2000s. It remains a stirring tribute popular at political events and Independence Day celebrations.
“Beer for My Horses”
The 2003 duet with Willie Nelson dominated country radio, reaching six weeks at number one on the Billboard chart. The rowdy song about hanging carousing troublemakers expresses a sort of renegade outlaw justice. Coming at the height of Toby’s popularity, “Beer for My Horses” further cemented his status as an icon of macho, southern-fried country music with crossover appeal. The song won the Academy of Country Music award for Vocal Event of the Year in 2004.
“As Good As I Once Was”
This 2005 single returned Toby to the top of the charts with its clever lyrics about a middle-aged man who has lost some of his youthful attributes but makes up for it with experience and wisdom. “As Good As I Once Was” spent six weeks at number one and featured a memorable music video starring Dennis Hopper as Toby’s adversary. It connected with male fans by mixing nostalgia for youth with a defiant refusal to act old, becoming one of Toby’s most downloaded digital tracks.
“Red Solo Cup”
Perhaps Toby’s most surprising viral hit song, 2011’s “Red Solo Cup” transformed the ubiquitous party cup into a country anthem. With its catchy, singalong chorus and toe-tapping melody, the tune is a fixture at tailgates, pregames, and raucous country concerts. Though silly and slight, the massive crossover success of “Red Solo Cup” demonstrated Toby Keith’s versatility and marketing savvy in the digital age. Despite mixed critical reviews, it has become a fan-favorite guilty pleasure.
“Made in America”
The patriotic 2012 single topped the country charts for four weeks and reestablished Toby as a voice of heartland pride and working-class values. Co-written by Bobby Pinson, “Made in America” pays tribute to Detroit auto workers, farmers, and other laborers who make the country run. Performed at both the Democratic and Republican National Conventions that year, this anthemic track resonated in an era of economic uncertainty and divisiveness. It’s become a sincere and emotional highlight of Toby’s live shows.
“Drinks After Work”
The title track from Toby’s 2013 album finds the singer drowning his sorrows after a breakup. It’s a classic country heartbreak ballad with clever wordplay, such as substituting “Neon Moon Pale Ale” for “Blue Moon.” “Drinks After Work” demonstrates Toby’s ability to blend traditional country songwriting with contemporary details. It reached number one on the country airplay chart, proving his knack for matching melancholic lyrics with an upbeat, radio-ready sound.
“Wacky Tobaccy”
On his later albums, Toby often includes humorous, tongue-in-cheek tunes that show off his silly side. One of the most noteworthy is 2017’s “Wacky Tobaccy,” a willowy folk-influenced ditty all about marijuana. Toby recorded it with the complicit Willie Nelson and Snoop Dogg, adding to the song’s ridiculous, let’s-get-high vibe. The creaky barbershop quartet harmonies and lyrics describing weed’s effects in euphemistic terms provide amusement while exemplifying Toby’s willingness to be in on the joke.
Key Takeaways
- Toby Keith’s career has been defined by rowdy patriotic anthems like “Courtesy of the Red, White and Blue,” nostalgic country ballads like “Should’ve Been a Cowboy,” and good-time party songs like “Red Solo Cup.”
- He is known for expertly blending contemporary and traditional sounds in a style that’s muscular, unapologetically patriotic, and distinctly Oklahoman.
- Massive crossover hits like “How Do You Like Me Now?!” and “Beer for My Horses” cemented his status as one of country music’s biggest stars in the 2000s.
- Later songs like “Made in America” and “Drinks After Work” prove his continued ability to put a contemporary spin on classic country songwriting themes.
- Toby’s catalog demonstrates versatility from patriotic pride to humor, heartbreak to nostalgia, delivered with his signature bravado.
Toby Keith’s Most Famous Songs By Genre
Patriotic Anthems
“Courtesy of the Red, White and Blue (The Angry American)”
“American Soldier”
“Made in America” “American Ride”
Heartbreak Ballads
“Who’s That Man”
“Wish I Didn’t Know Now”
“Drinks After Work” “She Never Cried in Front of Me”
Nostalgic Tunes
“Should’ve Been a Cowboy” “I Ain’t As Good As I Once Was”
“Get Out of My Car”
“A Little Too Late”
Party Songs
“How Do You Like Me Now?!”
“Beer for My Horses”
“Red Solo Cup”
“I Love This Bar”
Humorous Songs
“Weed with Willie”
“Wacky Tobaccy”
“I’ll Never Smoke Weed with Willie Again”
“Big Blue Note”
Frequently Asked Questions About Toby Keith’s Most Famous Songs
What was Toby Keith’s first big hit song?
Toby Keith’s first major hit song was 1993’s “Should’ve Been a Cowboy.” Released as his debut single, it went to #1 on the Billboard Country Songs chart and helped launch his career.
What Song Made Toby Keith Famous?
Toby Keith became famous for his hit song “Should’ve Been a Cowboy” which was released in 1993. The song was the lead single from his self-titled debut album and it reached #1 on the Billboard Hot Country Songs chart. Some key details about the song:
- The full title is “Should’ve Been a Cowboy” and it was written by Keith himself along with Ronnie Dunn.
- It has a very recognizable guitar intro and features Keith’s signature country vocals.
- Lyrically, it reminisces about being a cowboy out on the open range.
- It spent multiple weeks at #1 on the country charts and also crossed over to mainstream pop radio.
- It became Keith’s breakthrough hit and helped establish him as one of the biggest stars in country music in the 1990s.
- The song’s popularity led to Keith winning Top New Male Vocalist from the Academy of Country Music in 1994.
- It appears on numerous of Keith’s compilation and greatest hits albums over the years.
What is Toby Keith’s biggest crossover mainstream hit?
“How Do You Like Me Now?!” is considered Toby Keith’s biggest mainstream crossover hit. In addition to topping country charts for 5 weeks in 2000, it reached #31 on the overall Billboard Hot 100 chart.
What Toby Keith song became a patriotic anthem after 9/11?
In 2002, Toby released “Courtesy of the Red, White, and Blue (The Angry American)” as a patriotic response to the 9/11 terrorist attacks. It resonated strongly and helped cement his status as a leading voice of American patriotism.
What is Toby Keith’s highest-certified song?
“Beer for My Horses,” Toby’s 2003 duet with Willie Nelson, is certified Double Platinum by the RIAA. It sold over 2 million copies and is his highest certified single to date.
What comedy country song did Toby Keith record about marijuana?
In 2017, Toby released “Wacky Tobaccy,” a silly folk song filled with weed puns and euphemisms. Willie Nelson and Snoop Dogg featured on the humorous track about marijuana.